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I have no idea what the Fisherman's Wharf, Haight/Ashbury, or the Full House house are..
I cannot believe you have never heard of Fishermans Wharf or Haight/Ashbury. If so, it says more about you than the subject (not to be mean, but just honest, that displays lack of basic geographic and historic knowledge).
I'm aware that San Francisco also has Oakland in the area and a host of other decent sized, and Sacramento, for what its worth, isn't too much farther. Whereas Chicago just has itself and a lot of small suburbs and outlying cities, no other big cities for hours, closest would be Milwaukee, Indianapolis, and Detroit in that order, and none of them are that close. But is there something else?
I was just speaking from a cultural standpoint and what not. I think if you only compare cities, then Chicago is more cultural than San Francisco but the suburbs of San Francisco have a lot of ethnic goings on in them. However, a lot of the suburbs in Chicago, especially the northern and some western have a lot of that too (i.e. most of the Korean population in Chicago area actually now lives in the nearby northern suburbs whereas a few decades ago it was the city).
Most people worldwide could look at a photo taken anywhere within SF and be able to identify the city. It's very iconic, to the point where everyone knows what the skyline looks like, what the bridge looks like, what the hills and houses look like. Chicago, on the other hand, besides a photo that includes the Willis Tower or Cloudgate (AKA "Chicago Bean"), wouldn't be as identifiable. There just aren't very many dense cities with colorful Victorian architecture placed upon steep hills; SF is visually unique. Chicago, on the other hand, could arguably be more difficult to identify because its street level appearance is much more diverse. To the human mind, that interrupts our "mental imprint" of a city.
^ In that case, San Francisco is one of the most identifiable cities in the country at the very, very top.
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